7-Fluoro-2-methylquinazolin-5-amine → 4-(3-Fluoro-2-methoxyphenyl)-1-[(7-fluoro-2-methylquinazolin-5-yl)imino]-2-(trifluoromethyl)heptan-2-ol

Participants

Reaction Steps

In the same way as in Example 61, 228 mg (0.71 mmol) of 4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)heptanal, 150 mg (0.85 mmol) of 5-amino-7-fluoro-2-methylquinazoline and 0.5 ml of titanium tetraethoxide are reacted to give 4-(3-fluoro-2-methoxyphenyl)-1-[(7-fluoro-2-methylquinazolin-5-yl)imino]-2-(trifluoromethyl)heptan-2-ol. 185 mg of imine purified by column chromatography (silica gel, hexane/ethyl acetate 0-25%) are cyclized in the same way as in Example 61 at −20° C. with 3 ml (3 mmol) of 1 M boron tribromide solution to give the desired product. Column chromatography on silica gel (hexane/ethyl acetate 0-65%) yields 27 mg of product and 38 mg of the corresponding 5α,6α,8α) compound (Example 64).

Provenance & Evidence